Me and my girlfriend lived for 9 months in a tipi last year. From september to june. It was really nice to live in it. Even if it got down to -15C, it was no big problem as long as we had good clothes on, lots of wool. The open fire was very nice, it helped that we loved to chop a lot of wood. We had a pipe running into the base of the fire pit and made other improvements to keep smoke to a minimum. We checked the direction of wind all the time to put the smoke flaps in the right setup. But there's a downside, it's colder if the smoke goes out trough the hole quickly, we clearly noticed it's warmer if the smoke stays hanging above our heads and doesn't go away to fast. So we needed to find the right balance if we wanted to keep the heat in. We just didn't make the opening of the smoke flaps to big. A liner is also very important in a tipi, it had to be completely windproof so we didn't have a draft where we were sitting and sleeping. The floor was also important, we covered the earth with saw mill wood and over that a layer of spruce boughs. It made a noticable difference, and a nice floor to lie on next to the fire. Real luxury. Our best setup came after some months of living in it. We made three beds around the fire, which could be used to sit on, or sleep on. Firewood next to the door, food and other things in plastic boxes under the beds, which are off the floor. Cooking pots hanged on hooks tied to the anchor line, which kept the tipi down in strong winds.
The cold wasn't really a big problem in the tipi, but the worst part was actually when the mosquitos came in may. It became nearly unbearable to be in the tipi, as it was full of mosquitos. Making fire with a lot of smoke didn't seem an option as you don't really want a fire when it's too warm already.
We never had to transport the tipi, I would not be to happy to do so either. Except if I could chop some trees on the site to use as poles, I wouldn't want to transport those poles for any distance. The canvas itself was not too heavy for a 16 foot tipi.